UA105354C2 - Способ получения пентафторидов арилсеры - Google Patents
Способ получения пентафторидов арилсеры Download PDFInfo
- Publication number
- UA105354C2 UA105354C2 UAA200910470A UAA200910470A UA105354C2 UA 105354 C2 UA105354 C2 UA 105354C2 UA A200910470 A UAA200910470 A UA A200910470A UA A200910470 A UAA200910470 A UA A200910470A UA 105354 C2 UA105354 C2 UA 105354C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- substituted
- carbon atoms
- unsubstituted
- formula
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 claims abstract description 226
- -1 aryl sulfur compound Chemical class 0.000 claims abstract description 91
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 65
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 59
- 150000002367 halogens Chemical class 0.000 claims abstract description 57
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 153
- 125000004432 carbon atom Chemical group C* 0.000 claims description 108
- 150000001875 compounds Chemical class 0.000 claims description 101
- 229910052801 chlorine Inorganic materials 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 62
- 239000000460 chlorine Substances 0.000 claims description 59
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 58
- 150000002222 fluorine compounds Chemical class 0.000 claims description 54
- 229910052740 iodine Inorganic materials 0.000 claims description 41
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 37
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 150000002221 fluorine Chemical class 0.000 claims description 31
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 27
- 229910052794 bromium Inorganic materials 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 25
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 18
- 239000011630 iodine Substances 0.000 claims description 18
- 238000009835 boiling Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 13
- 230000003993 interaction Effects 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 230000000737 periodic effect Effects 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 9
- AECHPKVYOLOZLF-UHFFFAOYSA-N trifluoro(phenyl)-$l^{4}-sulfane Chemical compound FS(F)(F)C1=CC=CC=C1 AECHPKVYOLOZLF-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000005496 phosphonium group Chemical group 0.000 claims description 8
- 230000007704 transition Effects 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- ZZWBQKYJBWBAMW-UHFFFAOYSA-N (3-chloro-2,4,6-trifluorophenyl)-pentafluoro-$l^{6}-sulfane Chemical compound FC1=CC(F)=C(S(F)(F)(F)(F)F)C(F)=C1Cl ZZWBQKYJBWBAMW-UHFFFAOYSA-N 0.000 claims description 5
- UKZCHXGUSKYULA-UHFFFAOYSA-N CC(C)(C)C1=CC=C([S])C=C1 Chemical compound CC(C)(C)C1=CC=C([S])C=C1 UKZCHXGUSKYULA-UHFFFAOYSA-N 0.000 claims description 5
- JFBFGPWSYRHMIX-UHFFFAOYSA-N FC1=C(F)C(F)=C([S])C(F)=C1F Chemical compound FC1=C(F)C(F)=C([S])C(F)=C1F JFBFGPWSYRHMIX-UHFFFAOYSA-N 0.000 claims description 5
- PUKFPOUYXQFDGF-UHFFFAOYSA-N FC1=CC=C([S])C=C1 Chemical compound FC1=CC=C([S])C=C1 PUKFPOUYXQFDGF-UHFFFAOYSA-N 0.000 claims description 5
- NNEMXHIHSVAVRR-UHFFFAOYSA-N F[S](F)C1=CC=CC=C1 Chemical compound F[S](F)C1=CC=CC=C1 NNEMXHIHSVAVRR-UHFFFAOYSA-N 0.000 claims description 5
- KJNNNEWMELCQHV-UHFFFAOYSA-N [S]C1=CC=C(Br)C=C1 Chemical compound [S]C1=CC=C(Br)C=C1 KJNNNEWMELCQHV-UHFFFAOYSA-N 0.000 claims description 5
- RGQVZOJOYKFLTD-UHFFFAOYSA-N [S]C1=CC=C(Cl)C=C1 Chemical compound [S]C1=CC=C(Cl)C=C1 RGQVZOJOYKFLTD-UHFFFAOYSA-N 0.000 claims description 5
- SMGCISIIVCFOPD-UHFFFAOYSA-N [S]C1=CC=CC(Br)=C1 Chemical compound [S]C1=CC=CC(Br)=C1 SMGCISIIVCFOPD-UHFFFAOYSA-N 0.000 claims description 5
- CLMHJVKLDLZBGX-UHFFFAOYSA-N FC1=CC=CC=C1[S] Chemical compound FC1=CC=CC=C1[S] CLMHJVKLDLZBGX-UHFFFAOYSA-N 0.000 claims description 4
- PXWQUZXUFKFHSS-UHFFFAOYSA-N pentafluoro-(2,4,6-trifluorophenyl)-$l^{6}-sulfane Chemical compound FC1=CC(F)=C(S(F)(F)(F)(F)F)C(F)=C1 PXWQUZXUFKFHSS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- ICKMGODPGHREPV-UHFFFAOYSA-N pentafluoro-(2,3,4,5,6-pentafluorophenyl)-$l^{6}-sulfane Chemical compound FC1=C(F)C(F)=C(S(F)(F)(F)(F)F)C(F)=C1F ICKMGODPGHREPV-UHFFFAOYSA-N 0.000 claims description 3
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- SEEVXEHZKVVGNY-UHFFFAOYSA-N phenyl thiohypobromite Chemical compound BrSC1=CC=CC=C1 SEEVXEHZKVVGNY-UHFFFAOYSA-N 0.000 claims description 2
- VEUCZKAZCRSEMP-UHFFFAOYSA-N tert-butylsulfanylbenzene Chemical compound CC(C)(C)SC1=CC=CC=C1 VEUCZKAZCRSEMP-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- DEWWTGHYQYNHNW-UHFFFAOYSA-N ClC=1C(=C(C(=CC=1)F)[S])F Chemical compound ClC=1C(=C(C(=CC=1)F)[S])F DEWWTGHYQYNHNW-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 164
- 238000005481 NMR spectroscopy Methods 0.000 description 83
- 239000011541 reaction mixture Substances 0.000 description 70
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 56
- 239000000047 product Substances 0.000 description 42
- DMNYFEWFSFTYEL-UHFFFAOYSA-N pentafluoro(phenyl)-$l^{6}-sulfane Chemical compound FS(F)(F)(F)(F)C1=CC=CC=C1 DMNYFEWFSFTYEL-UHFFFAOYSA-N 0.000 description 38
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 description 36
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 18
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 18
- 229920002313 fluoropolymer Polymers 0.000 description 18
- 239000004811 fluoropolymer Substances 0.000 description 18
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 18
- 125000000129 anionic group Chemical group 0.000 description 17
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 125000005842 heteroatom Chemical group 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 238000001819 mass spectrum Methods 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 239000007789 gas Substances 0.000 description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 description 11
- 125000004434 sulfur atom Chemical group 0.000 description 11
- 229910001512 metal fluoride Inorganic materials 0.000 description 10
- 125000004430 oxygen atom Chemical group O* 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 9
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
- 239000011261 inert gas Substances 0.000 description 8
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 8
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 7
- FUHGRZYYJWLISV-UHFFFAOYSA-N F[Cl](F)(F)F Chemical class F[Cl](F)(F)F FUHGRZYYJWLISV-UHFFFAOYSA-N 0.000 description 7
- ORGROGADTAVCJL-UHFFFAOYSA-N [O-][N+](=O)C1=CC=C([S])C=C1 Chemical compound [O-][N+](=O)C1=CC=C([S])C=C1 ORGROGADTAVCJL-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- DVERFJXHCKPMNM-UHFFFAOYSA-N fluorophosphane Chemical compound PF DVERFJXHCKPMNM-UHFFFAOYSA-N 0.000 description 7
- NNYABWKWXRUWLH-UHFFFAOYSA-N FC1=CC=CC(F)=C1[S] Chemical compound FC1=CC=CC(F)=C1[S] NNYABWKWXRUWLH-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KJHXFHOJCCIKLD-UHFFFAOYSA-N 1-$l^{1}-sulfanyl-4-methylbenzene Chemical compound CC1=CC=C([S])C=C1 KJHXFHOJCCIKLD-UHFFFAOYSA-N 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000003682 fluorination reaction Methods 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- MFSRNICSILXXMS-UHFFFAOYSA-N pentafluoro-(4-methylphenyl)-$l^{6}-sulfane Chemical compound CC1=CC=C(S(F)(F)(F)(F)F)C=C1 MFSRNICSILXXMS-UHFFFAOYSA-N 0.000 description 5
- 150000004714 phosphonium salts Chemical class 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- 238000010189 synthetic method Methods 0.000 description 5
- SKRQTODWHDCMHZ-UHFFFAOYSA-N (3-chloro-2,6-difluorophenyl)-pentafluoro-$l^{6}-sulfane Chemical compound FC1=CC=C(Cl)C(F)=C1S(F)(F)(F)(F)F SKRQTODWHDCMHZ-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 150000002828 nitro derivatives Chemical class 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000011698 potassium fluoride Substances 0.000 description 4
- 235000003270 potassium fluoride Nutrition 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- RYKZGFBXDNZOCG-UHFFFAOYSA-N (2,6-difluorophenyl)-pentafluoro-$l^{6}-sulfane Chemical compound FC1=CC=CC(F)=C1S(F)(F)(F)(F)F RYKZGFBXDNZOCG-UHFFFAOYSA-N 0.000 description 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 3
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- RNRZLEZABHZRSX-UHFFFAOYSA-N diiodosilicon Chemical compound I[Si]I RNRZLEZABHZRSX-UHFFFAOYSA-N 0.000 description 3
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 3
- 230000035622 drinking Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- NCBOVAWEMBIIFK-UHFFFAOYSA-N (4-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=C(SCl)C=C1 NCBOVAWEMBIIFK-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- RPTQMFYXBSBPNM-UHFFFAOYSA-N 1-ethyl-2-[(2-ethylphenyl)disulfanyl]benzene Chemical compound CCC1=CC=CC=C1SSC1=CC=CC=C1CC RPTQMFYXBSBPNM-UHFFFAOYSA-N 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- JKIFPWHZEZQCQA-UHFFFAOYSA-N 2-nitrobenzenethiol Chemical class [O-][N+](=O)C1=CC=CC=C1S JKIFPWHZEZQCQA-UHFFFAOYSA-N 0.000 description 2
- BKMGLHQPYYCKPO-UHFFFAOYSA-N 2-tert-butylbenzenethiol Chemical compound CC(C)(C)C1=CC=CC=C1S BKMGLHQPYYCKPO-UHFFFAOYSA-N 0.000 description 2
- GNXBFFHXJDZGEK-UHFFFAOYSA-N 4-tert-butylbenzenethiol Chemical compound CC(C)(C)C1=CC=C(S)C=C1 GNXBFFHXJDZGEK-UHFFFAOYSA-N 0.000 description 2
- 101100177236 Bos taurus HBE4 gene Proteins 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- BZBWHGVIFWNYDA-UHFFFAOYSA-N [O-][N+](=O)[S](F)(F)(F)C1=CC=CC=C1 Chemical class [O-][N+](=O)[S](F)(F)(F)C1=CC=CC=C1 BZBWHGVIFWNYDA-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical class [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000005899 aromatization reaction Methods 0.000 description 2
- GPDDHWNFHNBPTC-UHFFFAOYSA-N chloro-tetrafluoro-phenyl-$l^{6}-sulfane Chemical compound FS(F)(F)(F)(Cl)C1=CC=CC=C1 GPDDHWNFHNBPTC-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007269 dehydrobromination reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- HJBZFPLBRXFZNE-UHFFFAOYSA-M tetrabutylphosphanium fluoride hydrofluoride Chemical compound F.[F-].CCCC[P+](CCCC)(CCCC)CCCC HJBZFPLBRXFZNE-UHFFFAOYSA-M 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- JDRNNVMPFUXWQD-UHFFFAOYSA-M tetraethylphosphanium;fluoride Chemical compound [F-].CC[P+](CC)(CC)CC JDRNNVMPFUXWQD-UHFFFAOYSA-M 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- VBHJAIGGLJOOLJ-UHFFFAOYSA-M tetramethylphosphanium;fluoride Chemical compound [F-].C[P+](C)(C)C VBHJAIGGLJOOLJ-UHFFFAOYSA-M 0.000 description 1
- GEPYJHDOGKHEMZ-UHFFFAOYSA-M tetraphenylphosphanium;fluoride Chemical compound [F-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GEPYJHDOGKHEMZ-UHFFFAOYSA-M 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical class C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- POSYVRHKTFDJTR-UHFFFAOYSA-M tetrapropylazanium;fluoride Chemical compound [F-].CCC[N+](CCC)(CCC)CCC POSYVRHKTFDJTR-UHFFFAOYSA-M 0.000 description 1
- XOGCTUKDUDAZKA-UHFFFAOYSA-N tetrapropylphosphanium Chemical compound CCC[P+](CCC)(CCC)CCC XOGCTUKDUDAZKA-UHFFFAOYSA-N 0.000 description 1
- RWBCVBNFUZGZHX-UHFFFAOYSA-M tetrapropylphosphanium;fluoride Chemical compound [F-].CCC[P+](CCC)(CCC)CCC RWBCVBNFUZGZHX-UHFFFAOYSA-M 0.000 description 1
- 230000035922 thirst Effects 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910021561 transition metal fluoride Inorganic materials 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- MVKCUESEARHECY-UHFFFAOYSA-N trifluoro-dimethyl-phenyl-$l^{6}-sulfane Chemical compound CS(C)(F)(F)(F)C1=CC=CC=C1 MVKCUESEARHECY-UHFFFAOYSA-N 0.000 description 1
- JBMKEQDNTMSWDF-UHFFFAOYSA-N trifluoro-dinitro-phenyl-$l^{6}-sulfane Chemical compound [O-][N+](=O)S(F)(F)(F)([N+]([O-])=O)C1=CC=CC=C1 JBMKEQDNTMSWDF-UHFFFAOYSA-N 0.000 description 1
- DACPZKWWOMDOFO-UHFFFAOYSA-N trimethyl(phenyl)-$l^{4}-sulfane Chemical compound CS(C)(C)C1=CC=CC=C1 DACPZKWWOMDOFO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Описаны новые способы приготовления пентафторидов арилсеры. Способы включают взаимодействие, по крайней мере, одного соединения арилсеры с галогеном и солью фтора с получением галотетрафторида арилсеры. Галотетрафторид арилсеры вводят в реакцию с источником фторида с получением целевого пентафторида арилсеры.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89666907P | 2007-03-23 | 2007-03-23 | |
| PCT/US2008/057849 WO2008118787A1 (en) | 2007-03-23 | 2008-03-21 | Process for producing arylsulfur pentafluorides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA105354C2 true UA105354C2 (ru) | 2014-05-12 |
Family
ID=39563574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200910470A UA105354C2 (ru) | 2007-03-23 | 2008-03-21 | Способ получения пентафторидов арилсеры |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US7592491B2 (ru) |
| EP (5) | EP2468719B1 (ru) |
| JP (2) | JP5447957B2 (ru) |
| KR (4) | KR20140061493A (ru) |
| CN (1) | CN101663268B (ru) |
| CA (4) | CA2680372C (ru) |
| RU (1) | RU2472779C2 (ru) |
| TW (1) | TWI327135B (ru) |
| UA (1) | UA105354C2 (ru) |
| WO (1) | WO2008118787A1 (ru) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7265247B1 (en) | 2006-07-28 | 2007-09-04 | Im&T Research, Inc. | Substituted phenylsulfur trifluoride and other like fluorinating agents |
| US8399720B2 (en) | 2007-03-23 | 2013-03-19 | Ube Industries, Ltd. | Methods for producing fluorinated phenylsulfur pentafluorides |
| EP2468719B1 (en) | 2007-03-23 | 2013-10-16 | UBE Industries, Ltd. | Process for producing arylsulfur pentafluorides |
| US8030516B2 (en) | 2007-10-19 | 2011-10-04 | Ube Industries, Ltd. | Methods for producing perfluoroalkanedi(sulfonyl chloride) |
| WO2009076345A1 (en) * | 2007-12-11 | 2009-06-18 | Im & T Research, Inc. | Methods and compositions for producing difluoromethylene-and trifluoromethyl-containing compounds |
| TW201006787A (en) * | 2008-03-07 | 2010-02-16 | Im & T Res Inc | Fluorination processes with arylsulfur halotetrafluorides |
| JP5439745B2 (ja) * | 2008-05-27 | 2014-03-12 | 宇部興産株式会社 | ハロゲノメチルペンタフルオロスルファニルベンゼン化合物及びその製造方法 |
| CA2734449A1 (en) * | 2008-08-18 | 2010-02-25 | Ube Industries, Ltd. | Methods for preparing fluoroalkyl arylsulfinyl compounds and fluorinated compounds thereto |
| KR101676054B1 (ko) * | 2008-09-22 | 2016-11-14 | 우베 고산 가부시키가이샤 | 폴리(펜타플루오로설파닐)방향족 화합물을 제조하기 위한 공정 |
| US20100174096A1 (en) * | 2009-01-05 | 2010-07-08 | Im&T Research, Inc. | Methods for Production of Optically Active Fluoropyrrolidine Derivatives |
| WO2010081014A1 (en) | 2009-01-09 | 2010-07-15 | Im&T Research, Inc. | Novel 4-fluoropyrrolidine-2-carbonyl fluoride compounds and their preparative methods |
| CZ303004B6 (cs) | 2010-10-07 | 2012-02-15 | Ústav organické chemie a biochemie Akademie ved CR v.v.i. | Zpusob prípravy substituovaných 3- a 4-(pentafluorsulfanyl)benzenu |
| EP2675785B1 (en) * | 2011-02-15 | 2018-04-11 | Ube Industries, Ltd. | Industrial methods for producing arylsulfur pentafluorides |
| CZ2011152A3 (cs) * | 2011-03-23 | 2011-11-16 | Ústav organické chemie a biochemie Akademie ved Ceské republiky, v.v.i. | Zpusob prípravy substituovaných nitrofenylsulfurpentafluoridu |
| WO2014062221A1 (en) | 2012-10-18 | 2014-04-24 | The Research Foundation For The State University Of New York | Aryl tetrafluorosulfanyl compounds |
| DE102013104346A1 (de) | 2013-04-29 | 2014-10-30 | Institute Of Organic Chemistry And Biochemistry As Cr, V.V.I. | Verfahren zur herstellung von arylschwefelpentafluoriden |
| US10676439B2 (en) * | 2015-11-25 | 2020-06-09 | Ube Industries, Ltd. | Pentafluorosulfanyl pyridine |
| CN110621658B (zh) * | 2017-02-28 | 2021-09-24 | 宇部兴产株式会社 | 五氟硫烷基芳香族化合物的制造方法 |
| JP2020518107A (ja) | 2017-04-26 | 2020-06-18 | オーティーアイ ルミオニクス インコーポレーテッドＯｔｉ Ｌｕｍｉｏｎｉｃｓ Ｉｎｃ． | 表面上のコーティングをパターン化する方法およびパターン化されたコーティングを含むデバイス |
| CN107389721B (zh) * | 2017-07-11 | 2019-05-03 | 西安科技大学 | 一种基于nmr技术快速定量中药活性组分的方法 |
| JP7205729B2 (ja) * | 2017-08-29 | 2023-01-17 | Ｕｂｅ株式会社 | ペンタフルオロスルファニル芳香族化合物の製造方法 |
| US11751415B2 (en) | 2018-02-02 | 2023-09-05 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
| EP3802488A1 (en) * | 2018-05-31 | 2021-04-14 | ETH Zurich | Method for preparing a polyfluorinated compound |
| JP7176256B2 (ja) * | 2018-07-05 | 2022-11-22 | トヨタ自動車株式会社 | フッ化物イオン電池及び非水系電解液 |
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